A dual-response mitochondria-targeted NIR fluorescent probe with large Stokes shift for monitoring viscosity and HOCl in living cells and zebrafish

Qu, Wangbo; Yang, Bin; Guo, Taiyu; Tian, Ruowei; Qiu, Shuang; Chen, Xinyue; Geng, Zhirong; Wang, Zhilin

doi:10.1039/d2an01693a

Cited by 7 publications

(4 citation statements)

References 67 publications

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“…[12,14] A xanthene-hemicyanine dye emitting at 654 nm was utilized to detect the HOCl through oxidation of the SÀ Me group in the presence of HOCl and monitor the emission changes. [15] A diarylbutadiene with pyridinium moiety emitting at 680 nm [16] and quinolinium moiety bearing a HOCl targeting moiety was used for targeting mitochondria and detecting HOCl. [17] Other fluorescent probes, includes derivatives of methylene blue [18] that showed turn-on emission upon interaction with HOCl were also developed.…”

Section: Introductionmentioning

confidence: 99%

Styryl‐NIR Mitochondrial Probes with Rapid HOCl Detection in Live‐Cells

et al. 2023

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Hypochlorous acid (HOCl) is critical for maintaining immune system balance, but it can harm mitochondria by hindering enzyme activity, leading to decreased ATP and increased cell death. In this study, we have designed a fluorophore with a pyridinium scaffold for selective staining of the mitochondria and to detect hypochlorite. The fluorophore exhibits strong solvatochromic emission due to intramolecular charge transfer and excellent sub-cellular localization in the mitochondria. Additionally, it shows a rapid response to HOCl with high selectivity among different reactive oxygen/nitrogen compounds with a detection limit of 2.31 μM. Moreover, it is also utilized for the exogenous and endogenous detection of HOCl in live cells, which may help study the role of hypochlorite in organelles at the cellular level. DFT and TDDFT calculations have been carried out to understand the relationship between the structure and properties of the cationic probes with respect to the α-cyano substitution and extension of π-conjugation. The selective detection of HOCl by C4 over other cationic probes has also been well-demonstrated, showing how the binding of HOCl affects the electronic properties of C4 through the analysis of non-bonding orbitals (NBO) population, electrostatic potential surface (ESP), and density of states (DOS) projected DOS investigations.

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Section: Introductionmentioning

confidence: 99%

Styryl‐NIR Mitochondrial Probes with Rapid HOCl Detection in Live‐Cells

et al. 2023

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“…In a nitrogen atmosphere, the reaction was carried out at 80 °C for 12 h. Then the reaction mixture was concentrated under reduced pressure and puried with a silica gel column (CH 2 Cl 2 / CH 3 OH = 20/1) to obtain probe 3, as a black crystal. The molecular structure of 3 was determined by 1 H NMR, 13 C NMR, LC-MS (Fig. S2-S4 †).…”

Section: Preparation and Characterization Of Probementioning

confidence: 99%

“…10,11 Fluorescence imaging as a powerful diagnostic tool has been widely employed for detection of analytes in biological systems due to its outstanding advantages such as good selectivity, high sensitivity, simplicity and real-time monitoring. 12,13 In recent years, a variety of uorescent probes for detecting HClO/ClO − have been designed based on specic oxidative cleavage of lactams, lactones or double bonds, oxidation of thioethers or selenides, and other specic oxidative reactions. [14][15][16][17][18] Among them, uorescent probes containing the conjugated olenic C]C double bond as the specic recognition site of ClO − has been utilized for the development of potential near-infrared (NIR) uorescence probes, which are more suitable for biological imaging application.…”

Section: Introductionmentioning

confidence: 99%

A facile ratiometric near-infrared fluorescent probe using conjugated 1,8-naphthalimide and dicyanoisophorone with a vinylene linker for detection and bioimaging of hypochlorite

Zhang

Huang

et al. 2023

Anal. Methods

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“…The following supporting information can be downloaded at https:// www.mdpi.com/article/10.3390/molecules28166055/s1. The document provides additional data, including synthesis protocols, 1 H NMR, 13 C NMR, HRMS ESI spectra, determination of quantum yield, detection limit, and stability in the presence of H 2 S [35,36,47,[68][69][70][71][72].…”

Section: Kinetic Studymentioning

confidence: 99%

A New and Fast-Response Fluorescent Probe for Monitoring Hypochlorous Acid Derived from Myeloperoxidase

2023

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Hypochlorous acid (HOCl) has been implicated in numerous pathologies associated with an inflammatory component, but its selective and sensitive detection in biological settings remains a challenge. In this report, imaging of HOCl was realized with a thiomorpholine-based probe as derivative of nitrobenzothiadiazole (NBD-S-TM). The fluorescence is based on photoinduced electron transfer by using nitrobenzothiadiazole core as a donor and thiomorpholine substituent as an acceptor. NBD-S-TM showed high sensitivity and a fast response to HOCl k = (2.6 ± 0.2) × 107 M−1s−1 with a 1:1 stoichiometry. The detection limit for HOCl was determined to be 60 nM. Furthermore, the desirable features of NBD-S-TM for the detection of HOCl in aqueous solutions, such as its reliability at physiological pH, rapid fluorescence response, and biocompatibility, enabled its application in the detection of HOCl in myeloperoxidase enzymatic system. Moreover, NBD-S-TM exhibited excellent selectivity and sensitivity for HOCl over other biologically relevant species, such as hydrogen peroxide and peroxynitrite. The fluorescent S-oxidized product (NBD-S-TSO) is only formed in the presence of HOCl. Probing with NBD-S-TM may be helpful to further the development of high throughput screening assays to monitor the activity of myeloperoxidase.

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A dual-response mitochondria-targeted NIR fluorescent probe with large Stokes shift for monitoring viscosity and HOCl in living cells and zebrafish

Abstract: Mitochondria are an important subcellular organelle involved in many cellular activities. Therefore, it is very important to monitor the concentration of various substances in mitochondria. In this work, we constructed...

Cited by 7 publications

References 67 publications

Styryl‐NIR Mitochondrial Probes with Rapid HOCl Detection in Live‐Cells

Styryl‐NIR Mitochondrial Probes with Rapid HOCl Detection in Live‐Cells

A facile ratiometric near-infrared fluorescent probe using conjugated 1,8-naphthalimide and dicyanoisophorone with a vinylene linker for detection and bioimaging of hypochlorite

A New and Fast-Response Fluorescent Probe for Monitoring Hypochlorous Acid Derived from Myeloperoxidase

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